Compositions and methods for controlling nematodes

Patent metadata

Field	Value
Publication number	US-9820486-B2
Application number	US-201615147247-A
Country	US
Kind code	B2
Filing date	May 5, 2016
Priority date	Feb 10, 2009
Publication date	Nov 21, 2017
Grant date	Nov 21, 2017

Abstract

Compositions and processes for controlling nematodes are described herein, e.g., nematodes that infest plants or animals. The compounds include oxazoles, oxadiazoles and thiadiazoles.

First claim

What is claimed is:

1. A method for the control of unwanted nematodes, the method comprising administering to a plant, a seed, or soil a composition comprising a compound of Formula VII or a salt thereof,

wherein,
A is aryl, arylalkyl, aryloxo, arylthio, heteroaryl, heteroarylalkyl, heteroaryloxo, or heteroarylthio, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of halo, C 1 -C 6 haloalkyl, C 6 -C 10 aryl, C 4 -C 7 cycloalkyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 6 -C 10 aryl(C 1 -C 6 )alkyl, C 6 -C 10 aryl(C 2 -C 6 )alkenyl, C 6 -C 10 aryl(C 2 -C 6 ) alkynyl, C 1 -C 6 hydroxyalkyl, amino, ureido, cyano, C 1 -C 6 acylamino, hydroxy, thiol, C 1 -C 6 acyloxy, azido, OCH 3 , OCF 3 , and C(H)O;
and
C is pyrrolyl, pyrrolyloxo, pyrrolythio, or pyrrolylalkyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of CH 3 , C 2 -C 10 alkyl, cycloalkyl, heterocycle, hydroxyalkyl, and halogen.

2. The method of claim 1 wherein A is optionally substituted aryl.

3. The method of claim 1 wherein C is optionally substituted pyrrolyl.

4. The method of claim 1 wherein the composition comprises a compound of Formula VIIa or a salt thereof,

wherein,
R 1 and R 5 are independently selected from the group consisting of hydrogen, CH 3 , F, Cl, Br, CF 3 and OCF 3 ;
R 2 and R 4 are independently selected from the group consisting of hydrogen, F, Cl, Br, and CF 3 ;
R 3 is selected from the group consisting of hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
R 6 , R 7 , R 8 and R 9 are independently selected from the group consisting of hydrogen, CH 3 , C 2 -C 10 alkyl, cycloalkyl, heterocycle, and halogen; and
X is a bond, CH 2 , O, or S.

5. The method of claim 4 wherein X is a bond.

6. The method of claim 4 wherein X is CH 2 .

7. The method of claim 1 wherein the composition comprises a surfactant.

8. The method of claim 1 wherein the composition comprises a co-solvent.

9. The method of claim 1 wherein the composition comprises one or more of an insecticide, a fungicide, an herbicide, or another pesticide.

10. The method of claim 9 wherein the composition comprises a pesticide selected from the group consisting of avermectin, ivermectin, milbemycin, imidacloprid, aldicarb, oxamyl, fenamiphos, fosthiazate, metam sodium, etridiazole, penta-chloro-nitrobenzene (PCNB), flutolanil, metalaxyl, mefenoxam, fosetyl-al, silthiofam, fludioxonil, myclobutanil, azoxystrobin, chlorothalonil, propiconazole, tebuconazole, pyraclostrobin, trifloxysulfuron, glyphosate and halosulfuron.

11. The method of claim 1 wherein the composition is applied to a seed.

12. A method for the control of unwanted nematodes, the method comprising administering to a plant, a seed, or soil a composition comprising a compound of Formula XII or a salt thereof,

wherein,
A is aryl or arylalkyl, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of halo, C 1 -C 6 haloalkyl, C 6 -C 10 aryl, C 4 -C 7 cycloalkyl, C 1 -C 6 alkyl, C 2 -C 6 alkenyl, C 2 -C 6 alkynyl, C 6 -C 10 aryl(C 1 -C 6 )alkyl, C 6 -C 10 aryl(C 2 -C 6 )alkenyl, C 6 -C 10 aryl(C 2 -C 6 ) alkynyl, C 1 -C 6 hydroxyalkyl, amino, ureido, cyano, C 1 -C 6 acylamino, hydroxy, thiol, C 1 -C 6 acyloxy, azido, C 1 -C 6 alkoxy and carboxy, and C(H)O; and
C is selected from the group consisting of thienyl, furanyl, oxazolyl, and isoxazolyl, each of which can be optionally independently substituted with one or more substituents selected from the group consisting of fluorine, chlorine, CH 3 , and OCF 3 ; and
X is CH 2 , O, or S.

13. The method of claim 12 wherein A is optionally substituted aryl.

14. The method of claim 12 wherein C is optionally substituted thienyl.

15. The method of claim 12 wherein the composition comprises a compound of Formula XIIa or a salt thereof,

wherein,
R 1 and R 5 are independently selected from the group consisting of hydrogen, CH 3 , F, Cl, Br, CF 3 , and OCF 3 ;
R 2 and R 4 are independently selected from the group consisting of hydrogen, F, Cl, Br, and CF 3 ;
R 3 is selected from the group consisting of hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
R 7 , R 8 and R 9 are independently selected from the group consisting of hydrogen, F, Cl, CH 3 , and OCF 3 ;
E is O or S; and
X is CH 2 , O or S.

16. The method of claim 12 wherein the composition comprises a compound of Formula XIIb or a salt thereof,

wherein,
R 1 and R 5 are independently selected from the group consisting of hydrogen, CH 3 , F, Cl, Br, CF 3 , and OCF 3 ;
R 2 and R 4 are independently selected from the group consisting of hydrogen, F, Cl, Br, and CF 3 ;
R 3 is selected from the group consisting of hydrogen, CH 3 , CF 3 , F, Cl, Br, OCF 3 , OCH 3 , CN, and C(H)O;
R 6 , R 8 and R 9 are independently selected from the group consisting of hydrogen, F, Cl, CH 3 , and OCF 3 ;
E is O or S; and
X is CH 2 , O or S.

17. The method of claim 12 wherein the composition comprises a surfactant.

18. The method of claim 12 wherein the composition comprises a co-solvent.

19. The method of claim 12 wherein the composition comprises one or more of an insecticide, a fungicide, an herbicide, or another pesticide.

20. The method of claim 19 wherein the composition comprises a pesticide selected from the group consisting of avermectin, ivermectin, milbemycin, imidacloprid, aldicarb, oxamyl, fenamiphos, fosthiazate, metam sodium, etridiazole, penta-chloro-nitrobenzene (PCNB), flutolanil, metalaxyl, mefenoxam, fosetyl-al, silthiofam, fludioxonil, myclobutanil, azoxystrobin, chlorothalonil, propiconazole, tebuconazole, pyraclostrobin, trifloxysulfuron, glyphosate and halosulfuron.

21. The method of claim 12 wherein the composition is applied to a seed.

22. The method of claim 12 wherein C is optionally substituted furanyl.

23. A method for the control of unwanted nematodes, the method comprising administering to a plant, a seed, or soil a composition comprising at least one compound selected from the group consisting of:
(a) a compound of Formula VII or a salt thereof,

wherein,
A is aryl, arylalkyl, aryloxo, arylthio, heteroaryl, heteroarylalkyl, heteroaryloxo, or heteroarylthio, each of which may be optionally independently substituted with one or more substituents selected from the group consisting of halo, C 1 -C 6 haloalkyl, C 6 -C 10 aryl, C 4 -C 7 cycloalkyl, C 1 -C 6 alkyl, C 2 -C 6 al

Assignees

• Monsanto Technology Llc

Inventors

• Slomczynska Urszula
• Dimmic Matt W
• Wideman Al
• Haakenson Jr William P

Classifications

• A61P33/10

  Anthelmintics · CPC title

• A01N43/82

  five-membered rings with three ring hetero atoms · CPC title

• C07D417/04

  directly linked by a ring-member-to-ring-member bond · CPC title

• A01N43/76

  1,3-Oxazoles; Hydrogenated 1,3-oxazoles · CPC title

• C07D413/04 Primary

  directly linked by a ring-member-to-ring-member bond · CPC title